I get to live in this property as a primary residence for free and have some extra cash flow every month.  

I lived in that house as my primary residence for 15 years.  

Everyone has different risk tolerance when investing but given that you are taking equity out of your primary residence extra caution is warranted.Hard money lenders are also an option but in that case the deal would need to be good enough to warrant the very high cost of capital.Best of luck.

I don't believe that many people on this site have been in that much of a financial bind (after all, no one would ever invest in real estate with negative cash flow), so it's going to take some creative traditional and non-traditional methods.

If you're talking owner occupied, meaning you're going to live there, it seems like choosing between those two areas is the primary consideration, then once you've picked that market you can dive down to consider specific properties.For your own personal residence, usually other life factors such as proximity to your place of employment and family considerations (spouse/partner, children, parents/extended family) are even more important than real estate investment.

I’m a little skeptical due to placing my primary residence on any kind of chopping block.

Talk to a traditional lender and see what you can afford then go from there.

I suppose that I can always rent out a spare bedroom in the primary half. 

If you can qualify for a traditional loan get pre-approved first. 

@Felicia Richardson I just went through the FHA duplex purchase process (closed about a week ago) and if you work with a lender experienced in FHA's it's not that difficult, really doesn't take much longer than a traditional mortgage.